Man upgrades Windows 1.0 to Windows 7 [video]

By Tom Warren, on 2nd Mar 11 5:18 pm with 98 Comments

Windows 1.0 to Windows 7

One man has captured every install of Windows from 1.0 through to 7 and shared it with the world via YouTube.

The video details install processes and the UI for each version of Windows over the past 25 years and most importantly the upgrade process. The only exception is Windows ME, missing as you can only upgrade to ME or 2000 and not both. The video creator, Andrew Tait, used VMWare to install each version and started by installing MS-DOS 5.0 to prepare for the Windows 1.0 installation. Monkey Island and Doom 2 are both installed to test upgrade compatibility throughout the years.

Microsoft first introduced Windows 1.0 on November 20, 1985. Since the introduction of Windows, the operating system has dominated the personal computer market. Microsoft’s market share worldwide for Windows currently sits at 91%, which is significantly higher than its rivals, Apple and Linux. Windows has seen a number of key changes throughout its life and the video (below) demonstrates the majority of these.

However, it hasn’t been all rosy over the past 25 years. Several run-ins with authorities worldwide have forced Microsoft to un-bundle key components of its operating system such as Internet Explorer and more recently Windows Media Player. A notorious court case with the American Department of Justice, which ended in 2001, saw Microsoft forced to share its systems, APIs source code and records with a specially allocated panel of experts. In the years after 2001 it also saw Microsoft un-bundling Internet Explorer from the Windows shell. Microsoft also got into trouble with the European Commission on several occasions. In 2003 the EU ordered Microsoft to provide a version of Windows without Windows Media Player, labeled Windows N. In January 2009 the EU also forced Microsoft to create a version of Windows without Internet Explorer. The company created the version, known as Windows 7 E, but later scrapped it in favor of a “browser ballot” screen that would allow consumers to pick their preferred browser.

If you’re a Windows fan and have 10 minutes free then check-out the nostalgic video below, thanks to The Next Web for spotting this classic.

  • Anonymous

    Man MS has been through some hurdles….

    • Joshua Greene

      And it keeps getting better with every release!

  • Bnlf

    haha nice work. someone has a lot of free time to play with old toys ;)

  • Grannyville7989

    Windows 98 was one of my favourite versions of Windows for games. And I don’t care who disagrees with me, Windows Vista is, and always will be, better than Windows XP.

    There I’ve said it. Now I’ll just wait for all of the hate to arrive in my inbox :)

    • astroX

      I agree with you, I never had a problem with Vista at all.

    • Tim Fox

      It was a great stepping stone. of course windows 7 is better because vista was the halfway mark. I never had problems with vista and sometimes miss it because of the great times I had in 07 with it

    • Anonymous

      win 98 is still the best system for games that I like. my alienware win7 cant play mechwarrior 4 or mechcommander 2 which were made my microsoft ..

    • Grannyville7989

      Ah, MechWarrior 2, Toy Story Activity Center, Star Wars: X-Wing vs. TIE Fighter and Recoil. Those were the games of my childhood

    • SirAnvil

      Did you know that MechTek released MW4 for free and it works on Win 7? (

    • Guest

      Yes, it is better.

    • Guest

      I still have a system running Vista. Runs stable.
      The performance score was better under Vista than W7!

    • Kanati

      That’s because they upped the limits in Win7 for the performance ratings. Has nothing to do with actual performance comparison between the two OS’. That said… never had a problem with vista after SP1. Before that it was flaky.

    • Guest

      hate? Sure, but you’ll have to pay first. Anyone who’ll pay for Vista will pay for their hate. ;-)

    • Anonymous

      I also had few problems with Vista. What helped was being late to the party (so all the drivers were ready when I switched) and getting it with a new laptop. I also read an article that explained what UAC was, and how it worked, and that helped a lot too. Why it is so annoying, what it does, and why to keep it (and I stuck with it, as it became less and less annoying). As a result, computing is safer. I think it was worth the annoyance.

    • Ddwornik

      I really like Win 7 UAC with the slider, don’t know if Vista has it.

      I use it, with pop-up, no dimming. I can still see the pop-up and think about it, but no risk of it showing in a presentation (it goes on left monitor). I’ve had issues with task manage + screen dimming in the past.

  • Chinonso

    Time sure does fly.

  • Chinonso

    Have been with Ms since win 98

  • Larry

    The chain is flawed. So it went DOS, windows 1, windows 2 (286/386 versions of those as well), 3.0, 3.1, 3.11 Windows for Work Groups, Win 95, Win 98, Win 98SE, Windows ME…..

    Around the same time as Windows 3.1 (16bit consumer) Windows NT 3.1 (32bit coporate focused) came out then NT 3.5, NT 3.51, NT 4.0 and Windows 2000 which was going to be called Windows NT 5.0 until the change at the last moment.

    Windows ME its plug and play, USB and consumer features were merged with Windows 2000 Kernel to make Windows XP. XP ended the dual paths. Everything was fully 32bit code. VS 2000 32bit and ME 16/32bit mix.

    • Vertuas

      Windows ME was missed out for a very good reason. A BSOD in the video would have been very embarassing (2 rs 1s? sho knows) indeed! ;o)

    • Starnamer

      The chain is *not* flawed. It’s the only sequence possible from end to end.

      If you try 1->2->3->95->98->ME you can’t upgrade any further and have to reinstall (in theory I think an ME->XP upgrade was supposed to be possible, but I don’t know of anyone who did it!).

      And you had to install NT3.5 as a fresh install and then go 3.5->3.51->4.0->2000…etc.

  • Steve Jobs

    Microsoft Windows is Amazing! Lets see what Apple could do with OSX?

    • Wfwef

      Go on, do an Apple one please

    • Wfwef

      Go on, do an Apple one please

    • forcer


  • twatface

    You skipped ME

    • Anonymous

      Yeah! That would have probably mucked up the process. Wow, talk about the complete opposite of a clean install.

    • Grannyville7989

      Windows ME came out after Windows 2000 which I don’t think you can perform an upgrade install on an NT system.

    • Jared

      I’d say ME was probably more popular in households though. 2K was very much targeted for businesses and especially networking. But around the time I remember most people I knew were either on 98 or ME.

    • SirAnvil

      Correct because ME is a Win98 upgrade code base and Win2K is an NT upgrade code base…

    • Hal

      Indeed, the (M)istake (E)dition would have been dangerous ;)

  • Arse

    I hate windows

    • Jackdevine

      Bring back cp/m and Gary Kildall

    • Steve Jobs

      Maybe you should go to instead of Winrumors! Or maybe you should go play with some iPad ported OS to computer OS!

  • winsux

    someone has a lot of time on their hands…

  • aforty

    Windows 2000 was my favorite version of Windows. So smooth, so clean. None of my games worked but I didn’t care and was one of my most visited sites as a result.

  • Anonymous

    Account user name @ 6:36. Haha.

  • Kanelp

    Neat video.

    My upgrade path (was a little more difficult with software compabilitiy) was
    C64 > C128 > A500 > A2000 > A4000 > Win95 > Win98 > Win2000 > WinXP > Win7 x64

    I didn’t have much problems with games in Windows 2000, but then again, all the games I had were at least Win95, since I was an Amiga user during the DOS to Win3 timeframe.

  • Rick

    I think he missed installing QEMM :)

  • Abcdef

    A “Windows fan”? Are there such things? Who could be a fan of such horrible junk?

    • Grannyville7989

      I am a fan of Windows, as well as a fan of Mac OS :)

    • Vertuas

      How can you not be a fan of Windows? its the only operating system (Windows NT) in existence writen from scratch rather than being based on Linux/ Unix / BSD or some other derivative from the 1960s

    • Crunch

      Unfortunately not ALL of it was written from scratch, early NT kernels allegedly used a ‘borrowed’ TCP/IP stack from BSD, which of course M$ denied, whilst still refusing to allow NT’s source to be viewed by anyone, even authorities, to prove it.

    • Not

      I think there is something called a COURT ORDER that would very much trump any of there objections IF there was ANY validity to code being “borrowed”….

    • Max534

      That’s really funny. So, you’re claiming that Microsoft didn’t borrow the BSD network stack? Just look at the .h files (included headers) for both solutions, and you’ll see.
      But, what the heck am asking for… this is not a Windows Fan’s forum, it’s the windows fanboys hydepark.

    • Br.Bill

      Er, AmigaDOS is not derivative of any other O/S. Original MacOS is from the ground up as well.

      What about BeOS?

    • Condor

      MacOS is based on BSD a Unix flavor

    • KeithBa

      At least half of the people that “liked” this run Windows on their system. Sad. Such mindless sheep.

    • Dolly

      More like 91%. Mindless sheep? Funny I think the same thing about iPhones, BMW’s, Starbucks, people who circle parking lots for 20 minutes looking for the closest spot, Hollister, American Idol, Twilight, street vernacular, tattoos, Facebook, loving/hating Justin Bieber’s hair, people who have time to reply to mindless sheep posts. You can find mindless sheep anywhere, the world is full of them especially on the hillsides of New Zealand. Now excuse me I have to go “like” this on Facebook, change the music in WMP, finish my Zune Marketplace downloads to my WP7 and complete this Word doc before lunch. Oh cool I’m doing all this WHILE Win7 SP1 is installing (a machine that has had XP, Vista, Vista SP1 and Win7) and I didn’t have to buy a whole new piece of hardware. Now where’s my Starbucks?

  • Daryl

    Did you pay for the license of all the versions installed?

  • David

    Windows ME was my favorite, he didn’t touch that one (or Bob!)

  • Djcarlsonjunk

    I still can’t get over the username “twatface”

  • Anonymous

    trip down memory lane (at least from win95->)
    nice username – ‘twatface’ :)

    w/r/t the pink color scheme – I remember w/ winXP MS touting the Luna theme and clean desktop – so they made a direct decision to force people to the new desktop layout. That trend must have carried through to Vista and 7.

    well done!


  • Reynardo

    There’s some old nightmares brought back. Now if only I could get Dungeon Keeper 1 to work on Vista… More seriously, I’m curious as to the hard drive requirements. Win 3.0 used to be on 5 floppy disks, and ran on a 20mb hard drive. I would have loved to hear the upgraded space and memory requirements as it went.

  • NickFitz

    “Since the introduction of Windows the operating system has dominated personal computers ever since.” – Utter rubbish (and the grammar is all wrong). Windows was a laughing stock until version 3.0, and it wasn’t until 3.11 (“for Workgroups”) that it really took off. I remember a friend telling me that he’d got a copy of Windows 2 from work. I asked “Are you going to install it on your own machine?” He looked at me and we both burst out laughing. The idea that one would install Windows 2 on anything other than a computer that belonged to somebody else was ludicrous.

  • wadsofat

    I think the clear winner of all this is VMware. Nice job emulating all that old hardware.

    • Andrew

      “I think the clear winner of all this is VMware. Nice job emulating all that old hardware.”

      I didn’t realize VMware emulated hardware, I thought it was just software.

    • Will

      Nope, it emulates ONLY hardware. You run software on top of the emulated hardware that VMWare provides.

    • Anonymous

      Actually VMware is virtualization. It does not emulate. And the hardware is the same. It hasn’t changed since the 80s. Still based on the same horrible Intel x86 architecture!

    • Telanis

      At least Intel tried to fix it with Itanium64, but noooo, AMD had to come along and make x86-64. Now it can suck with WORDs twice as big!

  • Suvankar 17


  • LD

    I’ve owned every one of those except Vista (skipped from xp to 7)

  • Inbredhick

    full upgrade compatibility for sure but it doesn’t take into account that the best computer from 30 years ago wouldn’t be able to handle later versions.

  • Sotiris Karagiannis

    I enjoyed the Video so much, I have gone through it as I have gone through my memory in all early years. It was a GREAT job you did there. Well done . It’s like listening to Rolling Stones again :)

  • Chris Zhang

    I just like playing games on Windows

  • slight

    Ok Doom is still running, but what about windows programs?
    A lot of win95 win98 programs don’t work on XP/Vista/7, if it work on XP, don’t work on win7 even with xp sp2 settings.

  • Wouter Heesakkers

    Man, this is NOT funny. I remember installing and working/playing with all the OS versions he has installed. This means I’m getting old to.

  • Dude

    Windows… Fan…? Those exist? What a joke.

    • Grannyville7989

      Yup, I sure do exist :)

    • Guest

      Dude . why are you on a WInRumours site… yes I do like windows!!! and I am a fan

    • Flurn

      Yep, windows fans exist, evolutionary dead ends they may be, but they do exist.

  • Windows is for losers

    What is the purpose of this? They should be applauded for 23 years of application compatibility? WHY?! Who gives a shit if Doom 2 for DOS still runs? Rather than being so concerned with running ancient apps that have modern equivalents (there are even native non-DOS versions of Doom 2 around), perhaps they should focus on making an OS that doesn’t give you hemorrhoids and ulcers. Man, Windows sucks so hard. People paying attention switched to the Mac or Linux in like 2003.

  • Windows is for losers

    What is the purpose of this? They should be applauded for 23 years of application compatibility? WHY?! Who gives a shit if Doom 2 for DOS still runs? Rather than being so concerned with running ancient apps that have modern equivalents (there are even native non-DOS versions of Doom 2 around), perhaps they should focus on making an OS that doesn’t give you hemorrhoids and ulcers. Man, Windows sucks so hard. People paying attention switched to the Mac or Linux in like 2003.

    • Scientificbob

      Companies who have payed hundreds of thousands of dollars to software engineers for developping professional custom software care.
      Contrary to why you seem to think, companies don’t like it to have to reïnvest in software development everytime a new version of the OS is released.

      Go waste your money on your 4th smartphone in 2 years and shut up.

    • Alan L.

      We run Linux for our scada systems, but we still have to use Windows to collect data via OPC. As far as I know, there is no process control software that runs on Apple’s OS.

    • Grannyville7989

      I’m a loser? AWESOME!

      Sent from my MacBook Pro running Windows 7

  • Muluck


  • Tom

    “Microsoft’s market share worldwide for Windows currently sits at 91%, which is significantly higher than its rivals, Apple and Linux.”

    It’s like saying that elephant is significantly heavier than the mouse.

  • Peter Weyant

    Wow, my life for the past 25 years just passed before my eyes, with about 4 reboots per upgrade – and at least one or two rebuilds. Oh wait, my mistake – I did not go to Win7 last year – went to Ubuntu. No wonder I am not on year 26 with upgrades LOL.

    • Grannyville7989


  • Christopher Walsh

    I’ve been around since DOS 3. 286 FTW!

  • Anonymous Coward

    I wont bother feeding the Trolls,

    A very interesting piece showing the various versions. I do think that ME was the achillies heel in the whole windows ecosystem as you had nowhere to go from ME as XP required a full re-install.

    But for an experiment it worked very well, kudos to you for doing it and, regardless of the detractors, Microsoft, as a purveyor of operating systems, has managed to do it longer than anyone else other than UNIX.

  • Odegaard

    I don’t see the relevance of the couple of court cases through out the years to this video?!? Seems like the journalist beat the commenters to the trolling.

  • Brucbn

    what a bout BOB ?

  • Theorysans

    I take issue with this sentence from the article:

    “Since the introduction of Windows, the operating system has dominated the personal computer market.”

    That’s inaccurate. Windows 1.0, Windows 2.0 and Windows 3.0 were abject failures. It wasn’t until Windows 3.1 that companies began install the OS on a large scale.

  • Tim Wood

    Kudos to Andrew T. for the video; good technical work, snappy editing and fun. But, did he obtain a synchronization license from the publisher of “Chain of Fools” and from Aretha Franklin’s record company to use the song? Just’ askin’.

  • Guru

    Great Job, loved the video!

  • luber

    how fast Doom starts on Win7 in compare with Win 3.1?

  • Justin Kimbrell

    I hate windows with a passion, but only after using it for 15 years. It’s these very reasons I choose other platforms. I would rather not have 23 years of compatibility. It’s not a bad thing to scratch the design of everything you have done for the last decade just to see how much better it could become.

    I’m not trolling folks. Seriously cool video, and thoroughly enjoyed the post. It definitely brought back memories thinking “Wow, this is the coolest thing I have ever seen.”

  • Guest

    Windows has it flaws and its grands i don’t know why to hate it, Its no like mac or ubuntu (don’t know other versions of linux) is perfect or anything. All the apps that i need works on windows. I have a mac and i love it too and i use linux on VB to program and it is great. Why fight for who is the best when you can easily use all of then!!!

  • Ray Charbonneau

    Fun, especially if you imagine the narrator is Roy from “The IT Crowd”

  • Max Allan

    The important question is : Do all the promised improvements in speed/etc.. appear. Every time I install Windows I sit there looking at the pop ups “Your computer will now run faster” “…start quicker” “…crash less” and think “Really, or is it just coz I had to upgrade my hardware again?”

    • drewmeister


  • Chaminda de Silva

    I never had a problem with Windows Vista after I stopped using it :o)

  • Bob

    Nice going, and for those Microsoft haters, this is what I call Customer centric :-) and not techy centric

  • Don

    Thanks for the memories!

  • Tkandala

    Great job there.. It’s been like traveling in a time machine from past to present and I really enjoyed it..

  • Rorypoole_1999

    I think you can make program groups in windows 1 and 2

  • Max534

    This is so cool, I’m gonna try this myself:)
    Oh wait… I don’t own all these systems :(
    Nevertheless, it was a fun to watch.